Hydrochloric Acid → Methyl(2-pyridylmethyl)amine

HRID 1600388Notes

Reaction equation

HRID 1600388 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=O.[BH4-].[Na+].Cl>C(O)C.ClCCl.C1C=CC=CC=1>[CH3:1][NH:2][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 88757Methyl(2-pyridylmethyl)amineYield 85%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methylamine gas was bubbled through the benzene solution(60 ml) of 10.7 g(100 mmol) of 2-pyridinecarboxaldehyde for 2 hours. Benzene was distilledoff under a reduced pressure and the residue was taken up in 40 ml of ethanol. To the resulting solution was added 5.7 g of NaBH4 in three portions and the resulting mixture was stirred at room temperature for 8 hours. To the reaction mixture was added 0.5N hydrochloric acid with care not to allow the pH below 6. 300 ml of dichloromethane was added thereto and the resulting solution was washed three times with 1M NaHCO3 solution of pH 10. The organic layer was concentrated under a reduced pressure to give 10.4 g of the title compound(yield: 85%).

Workup

  1. washthe resulting solution was washed three times with 1M NaHCO3 solution of pH 10
  2. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-32e646aa95fe421fab4c49c31b80c576
Source dataset
uspto-grants-1998_04
Patent number
US05744621

Reaction notes

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